4 day itinerary to Chicago with Kids

Chicago was our first road trip as a family of four. The third most populated city in the US, behind New York and Los Angeles, we couldn’t resist the culture, architecture, and city life of Chicago and we were excited to explore a new city. With our youngest daughter just over 9 months old and a 2 year old toddler full of energy in tow, we didn’t know what to expect. We headed out early and drove 9 hours to our destination and considering the distance of our drive, it went off without a hitch. The girls slept for most of the trip and for the other times we kept them occupied with snacks, toys, books, and music.

From the navy pier, north beach, Millennium Park, and their renown museums, there were plenty of things to see and do in Chicago.

Here are our highlights of Chicago in 4 days:

Day 1: North Beach and Wrigley Stadium

North Beach:
Grab your swim suits, towels, buckets and shovels, North Beach is a great place to soak in the sun during the warmer months and enjoy a leisurely stroll along their boardwalk. A 15 minute drive north of downtown Chicago, just be prepared that this area may be packed on the weekends so best to head out early. Parking is available within the vicinity. After exploring the beach area, head over to Castaways for a great place to grab a bite to eat on their rooftop.

Chicago Cubs Wrigley Stadium:
Whether you are a fan of the Cubs or not, catch a baseball game at the historic Wrigley Stadium. The stadium is rich in history, and is said to be the second oldest baseball field which first opened in 1914. Wrigley Field is home to one of 2 baseball teams in Chicago, the Chicago Cubs. Located 15 minutes from North Beach and half hour to downtown Chicago. Tours are available for those baseball fanatics wishing to enrich them self with not just the history of the team but the many decades of baseball’s stories itself. The atmosphere and fans in this stadium, is said to be one of the most passionate and energetic.

Day 2: Millennium Park, Pritzker Pavillion, Magnificent Mile, 360 Chicago (Formerly John Hancock Center)

Millennium Park and Surrounding Area

Start your morning off and drop by the highly recommended breakfast cafe, at the Wildberry Pancake & Cafe. The pancakes are definitely their specialty but alternate breakfast options are also available.

The Millennium Park is a popular place for tourists and locals and a great place for families to spend most of the day. Your first photo opportunity is a stop at Chicago’s most popular tourist attraction the Cloud Gate, aka The Bean for its unique bean-like shape. Don’t forget to try different shot angles with the bean,as its made of material that produces many reflective properties, and can provide some cool photo perspectives.

Aside from the Cloud Gate, the other popular attractions within the park also include the Crown Fountain (a video art structure, of various faces streaming a small fountain on to spectators passing by.), Lurie Gardens – stop and smell the roses (when in season), the Art Institute of Chicago, and the Millennium Monument.

The Cloud Gate aka “The Bean”

Pritzker Pavillion

The Crown Fountain

State Street and Magnificent Mile
A shoppers haven, both State St and Magnificent Mile offer many popular major department stores along this strip: from Nordstrom, TJ Maxx, Target, Forever 21 and Macy’s. Along State Street, you will come across the iconic Old Chicago Theater. The theater is nearly 100 years old, but has managed to maintain its original charming architecture. The best way to get around the city is by foot. You will learn to appreciate the distinct neighborhoods within the various area.
Your visit to Chicago would not be complete with out a visit to one of the popular deep dish pizza eateries in town. We stopped by to try Lou Malnati’s pizzeria restaurant in the area. Set aside at least close to 2 hours, as it takes up to 45 minutes to cook a deep dish pizza.

360 Chicago (formerly John Hancock Center)
The Observation tower offers the most breathtaking views of the city’s skyline and also a unique experience for more adventure goers, the TILT ride – an enclosed moving platform that gives you an in your face perspective of the city. Click here to view the hours of operation and costs of admission tickets.

360 Chicago (or formerly John Hancock Center)

Day 3: Navy Pier, Kenzie Bridge, and Architecture river cruise

The architectural river cruise was one of the highlights of our trip. The cruise itself is about 1.5 hours and tends to be quite popular during the peak months. I would highly recommend booking the tickets in advance for this tour, as they tend to sell out. The tour offers an on-board tour guide, including a commentary about the history of Chicago’s architecture and a few hidden gems in the city. A night cruise option is also available. Click here for ticket prices and options. You can capture many great photo opportunities of Chicago’s many structures and buildings from a fresh new perspective.

The Navy Pier
Another of Chicago’s many landmarks in the city, known for its many shops, restaurants, and amusement park. During our visit, the renovations were underway to re-design the space and provide more efficiency in the area. Major improvements were also coming for the popular Ferris wheel ride, but we still had an opportunity to ride it before they will official retire it. (Last update: it was retired on September 27, 2015). There is no cost to enter the Navy Pier, however rides were of extra cost as well as any other special exhibits.

The Silver Palm Restaurant
Located about 12 minutes west of the downtown core, we headed to one of Anthony Bourdain’s recommended restaurants, from his tv show “No Reservations”, The Silver Palm Restaurant. The front end of the restaurant is a typical dining establishment but towards the back is a connecting old railroad car and such a cool and unique setting in itself. A decent selection of entree’s, burgers, and sandwiches are available. We tried what he declared to be “the greatest sandwich in America” called the three little pigs: filled with smoked ham, a breaded pork cutlet, two strips of bacon, and two fried eggs, blanketed in a thick coat of gruyere, all on a brioche bun. Quite a big portion for a single person to eat but enough to satisfy anyone’s hunger, especially after a long day of exploring.

Kenzie Bridge

Day 4: Buckingham Fountain, Field Museum, and Planetarium

The Adler Planetarium
The Planetarium is great for little explorers to learn about our solar system and astronomy in general. There is a dedicated little explorers section for younger children where they can interactively climb, crawl, run, and simulate a mission to outer space.
Click here for prices and hours of operations to the Planetarium.

The Field Museum of Natural History
The Museum is home to the world’s largest (most complete and well preserved) T-Rex, named Sue after its discoverer. The museum is quite vast, and is considered to be one of the largest in the world. From pre-historic, to ancient times, and to present time, there are many exhibits and artifacts that will fulfill’s your little ones curiosities. Click here to purchase your tickets in advance. Children 2 and under are free.

The Buckingham Fountain
The fountain is located approximately in the middle of Grant Park Rose Gardens. The light show is daily, every hour from dusk until 10pm, between mid-April to mid-October, depending on the weather. The show will last about 20 minutes.